(μ3-Trithio­cyanurato-κ6N1,S2:N3,S4:N5,S6)tris­[(N,N,N′,N′′,N′′-penta­methyl­diethylenetriamine-κ3N,N′,N′′)zinc(II)] tris­(perchlorate)

Marek, J.; Trávníček, Z.; Čermáková, Š.

doi:10.1107/S1600536807016595

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(μ₃-Trithiocyanurato-κ⁶N¹,S²:N³,S⁴:N⁵,S⁶)tris[(N,N,N′,N′′,N′′-pentamethyldiethylenetriamine-κ³N,N′,N′′)zinc(II)] tris(perchlorate)

J. Marek, Z. Trávníček and Š. Čermáková

In the title compound, [Zn₃(C₃N₃S₃)(C₉H₂₃N₃)₃](ClO₄)₃, the three Zn^II centres, related by the body-diagonal threefold symmetry along [111], are bridged by a trithiocyanurate(3−) anion (ttc), with each centre having a distorted trigonal–bipyramidal geometry and bonded by three N atoms of a tridentate N,N,N′,N′′,N′′-pentamethyldiethylenetriamine ligand, and one S and one N atoms of the ttc ligand. The secondary structure is stabilized by a variety of non-bonding C—H

O interactions, connecting the cation and perchlorate anions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807016595/bx2070sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807016595/bx2070Isup2.hkl Contains datablock I

CCDC reference: 648058

checkCIF report

Key indicators

Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.004 Å
Disorder in main residue
R factor = 0.023
wR factor = 0.076
Data-to-parameter ratio = 24.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT410_ALERT_2_B Short Intra H...H Contact  H4B    ..  H3A1    ..       1.83 Ang.
PLAT432_ALERT_2_B Short Inter X...Y Contact  O20    ..  C7A     ..       2.89 Ang.
PLAT432_ALERT_2_B Short Inter X...Y Contact  O20    ..  C7A     ..       2.89 Ang.
PLAT432_ALERT_2_B Short Inter X...Y Contact  O20    ..  C7A     ..       2.89 Ang.
PLAT480_ALERT_4_B Long H...A H-Bond Reported H7A    ..  O10     ..       3.04 Ang.

Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.71
PLAT141_ALERT_4_C su on a - Axis Small or Missing (x 100000) .....         16 Ang.
PLAT213_ALERT_2_C Atom C6A     has ADP max/min Ratio .............       3.30 prola
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl2
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl3
PLAT301_ALERT_3_C Main Residue  Disorder .........................      24.00 Perc.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2A    ..  O17     ..       2.85 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7A    ..  O17     ..       2.91 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2D    ..  O17     ..       2.97 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2D    ..  O17     ..       2.97 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7F    ..  O17     ..       2.94 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7F    ..  O17     ..       2.94 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6A2   ..  O10     ..       2.67 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5B    ..  O18     ..       2.79 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10B   ..  O10     ..       2.69 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2A    ..  O17     ..       2.68 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8C    ..  O16     ..       2.83 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7C    ..  O20     ..       2.71 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7E    ..  O20     ..       2.61 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7C    ..  O20     ..       2.71 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7C    ..  O20     ..       2.71 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7C    ..  O20     ..       2.71 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7C    ..  O20     ..       2.71 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7F    ..  O10     ..       2.78 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5B    ..  O18     ..       2.79 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4B    ..  O10     ..       2.61 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5B    ..  O18     ..       2.79 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10C   ..  S       ..       2.98 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C7     ..  O17     ..       3.75 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C2A    ..  O17     ..       3.81 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C2A    ..  O17     ..       3.81 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C7A    ..  O17     ..       3.77 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C7A    ..  O17     ..       3.77 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C7     ..  O10     ..       3.77 Ang.
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C7A    ..  O20     ..      96.40 Deg.
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      61.00 A   3 
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          9
            N3  -ZN  -N1  -C1    178.40  0.40   1.555   1.555   1.555   9.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         14
            N3  -ZN  -N1  -C1      3.80  0.60   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         19
            N1  -ZN  -N3  -C8     11.30  0.60   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         24
            N1  -ZN  -N3  -C3   -107.80  0.60   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         29
            N1  -ZN  -N3  -C4    132.50  0.50   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         34
            N1  -ZN  -N3  -C3A  -118.20  1.50   1.555   1.555   1.555   1.555
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          5
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      10.00 Deg.
              C3   -N3   -C3A     1.555   1.555   1.555

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.710
            Tmax scaled      0.710 Tmin scaled      0.589
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           31.53
           From the CIF: _reflns_number_total               5689
           Count of symmetry unique reflns         3141
           Completeness (_total/calc)            181.12%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2548
           Fraction of Friedel pairs measured     0.811
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   5 ALERT level B = Potentially serious problem
  44 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
  42 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL023_ALERT_1_A There is a mismatched ^ on line 247
              cavities are at a distance of 3.8 \%A from S1, and their volume is 63(6) \%A^3
              If you require a ^ then it should be escaped
              with a \, i.e. \^
              Otherwise there must be a matching closing ~, e.g. ^12^C
PUBL023_ALERT_1_A There is a mismatched ^ on line 248
              ^(Spek, 2003). The secondary structure of (I) is stabilized by a variety of
              If you require a ^ then it should be escaped
              with a \, i.e. \^
              Otherwise there must be a matching closing ~, e.g. ^12^C

   2 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Johnson & Burnett, 1996), VMD (Version 1.8.5; Humphrey et al., 1996) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2003) and DIAMOND.

µ₃-Trithiocyanurato-κ⁶N¹,S²:N³,S⁴:N⁵,S⁶)tris[(N,N,N',N'',N''- pentamethyldiethylenetriamine-κ³N,N',N'')zinc(II)] tris(perchlorate) top

Crystal data top

[Zn₃(C₃N₃S₃)(C₉H₂₃N₃)₃](ClO₄)₃	D_x = 1.519 Mg m⁻³
M_r = 1188.61	Mo Kα radiation, λ = 0.71073 Å
Cubic, P2₁3	Cell parameters from 29540 reflections
Hall symbol: P 2ac 2ab 3	θ = 2.6–31.9°
a = 17.32348 (16) Å	µ = 1.71 mm⁻¹
V = 5198.83 (8) Å³	T = 120 K
Z = 4	Prism, light yellow
F(000) = 2472	0.30 × 0.30 × 0.20 mm

Data collection top

Kuma KM-4 CCD diffractometer	5689 independent reflections
Radiation source: fine-focus sealed tube	5055 reflections with I > 2σ(I)
Enhance (Oxford Diffraction) monochromator	R_int = 0.030
Detector resolution: 8.3611 pixels mm^-1	θ_max = 31.5°, θ_min = 2.6°
rotation method ω scans	h = −25→24
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −25→24
T_min = 0.829, T_max = 1.000	l = −19→24
39533 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.023	H-atom parameters constrained
wR(F²) = 0.076	w = 1/[σ²(F_o²) + (0.04P)² + 5P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.002
5689 reflections	Δρ_max = 0.71 e Å⁻³
231 parameters	Δρ_min = −0.61 e Å⁻³
51 restraints	Absolute structure: Flack (1983), 2548 Friedel pairs????
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.028 (9)

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Zn	0.419995 (14)	0.516862 (14)	0.699755 (14)	0.01156 (5)
S	0.53343 (3)	0.44064 (3)	0.68618 (3)	0.01656 (10)
N1	0.49252 (10)	0.55834 (11)	0.60370 (10)	0.0120 (3)
N3	0.36170 (11)	0.46361 (11)	0.79620 (11)	0.0162 (3)
N4	0.41749 (11)	0.61749 (11)	0.76602 (11)	0.0147 (3)
C1	0.54595 (12)	0.50127 (12)	0.60926 (12)	0.0119 (4)
N2	0.3247 (5)	0.4813 (3)	0.6358 (4)	0.0158 (5)	0.758 (6)
C2	0.26318 (17)	0.46627 (19)	0.69358 (19)	0.0192 (7)	0.758 (6)
H2A	0.2216	0.4354	0.6695	0.023*	0.758 (6)
H2B	0.2407	0.5159	0.7108	0.023*	0.758 (6)
C6	0.2962 (2)	0.5385 (2)	0.5786 (2)	0.0220 (7)	0.758 (6)
H6A	0.3363	0.5479	0.5398	0.033*	0.758 (6)
H6B	0.2838	0.5869	0.6050	0.033*	0.758 (6)
H6C	0.2499	0.5183	0.5532	0.033*	0.758 (6)
C7	0.3442 (2)	0.4094 (2)	0.5930 (2)	0.0243 (8)	0.758 (6)
H7A	0.2996	0.3931	0.5622	0.036*	0.758 (6)
H7B	0.3576	0.3686	0.6298	0.036*	0.758 (6)
H7C	0.3882	0.4192	0.5588	0.036*	0.758 (6)
C3	0.2948 (6)	0.4235 (6)	0.7623 (8)	0.0220 (14)	0.758 (6)
H3A	0.2539	0.4184	0.8018	0.026*	0.758 (6)
H3B	0.3105	0.3710	0.7462	0.026*	0.758 (6)
N2A	0.3284 (15)	0.4757 (11)	0.6331 (11)	0.0158 (5)	0.242 (6)
C2A	0.2955 (5)	0.4129 (6)	0.6810 (5)	0.019 (2)	0.242 (6)
H2C	0.3298	0.3672	0.6778	0.023*	0.242 (6)
H2D	0.2446	0.3979	0.6596	0.023*	0.242 (6)
C6A	0.2721 (6)	0.5384 (6)	0.6187 (7)	0.018 (2)	0.242 (6)
H6A1	0.2989	0.5830	0.5964	0.028*	0.242 (6)
H6A2	0.2477	0.5535	0.6674	0.028*	0.242 (6)
H6A3	0.2325	0.5203	0.5826	0.028*	0.242 (6)
C7A	0.3531 (7)	0.4448 (8)	0.5571 (6)	0.025 (3)	0.242 (6)
H7D	0.3902	0.4028	0.5650	0.037*	0.242 (6)
H7E	0.3774	0.4861	0.5270	0.037*	0.242 (6)
H7F	0.3080	0.4252	0.5292	0.037*	0.242 (6)
C3A	0.285 (2)	0.435 (2)	0.766 (3)	0.0220 (14)	0.242 (6)
H3A1	0.2457	0.4758	0.7707	0.026*	0.242 (6)
H3A2	0.2682	0.3895	0.7959	0.026*	0.242 (6)
C4	0.34006 (16)	0.52884 (15)	0.84668 (15)	0.0238 (5)
H4A	0.3326	0.5101	0.9001	0.029*
H4B	0.2908	0.5516	0.8287	0.029*
C5	0.40265 (17)	0.58963 (15)	0.84537 (14)	0.0243 (5)
H5A	0.3870	0.6337	0.8783	0.029*
H5B	0.4508	0.5677	0.8670	0.029*
C8	0.40848 (17)	0.40694 (16)	0.83884 (16)	0.0278 (6)
H8A	0.3774	0.3842	0.8803	0.042*
H8B	0.4536	0.4327	0.8611	0.042*
H8C	0.4256	0.3662	0.8035	0.042*
C9	0.49266 (15)	0.65720 (15)	0.76223 (15)	0.0229 (5)
H9A	0.4937	0.6993	0.8000	0.034*
H9B	0.5003	0.6782	0.7103	0.034*
H9C	0.5340	0.6204	0.7739	0.034*
C10	0.35664 (15)	0.67283 (14)	0.74185 (15)	0.0222 (5)
H10A	0.3584	0.7186	0.7751	0.033*
H10B	0.3059	0.6482	0.7464	0.033*
H10C	0.3654	0.6882	0.6881	0.033*
Cl2	0.06414 (3)	0.43586 (3)	0.56414 (3)	0.01806 (17)
O17	0.13816 (11)	0.42569 (14)	0.52828 (12)	0.0323 (5)
O18	0.01621 (12)	0.48379 (12)	0.51621 (12)	0.0376 (8)
Cl1	0.30230 (3)	0.19770 (3)	0.80230 (3)	0.01537 (15)
O15	0.35014 (10)	0.14986 (10)	0.85014 (10)	0.0242 (6)
O16	0.24410 (10)	0.15086 (10)	0.76522 (10)	0.0215 (3)
Cl3	0.14408 (3)	0.64408 (3)	0.85592 (3)	0.01791 (17)
O10	0.10382 (12)	0.71440 (11)	0.83772 (12)	0.0295 (4)
O20	0.09628 (13)	0.59628 (13)	0.90372 (13)	0.0383 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn	0.01025 (11)	0.01278 (11)	0.01166 (11)	0.00039 (8)	0.00095 (8)	−0.00012 (8)
S	0.0153 (2)	0.0174 (2)	0.0170 (2)	0.00497 (18)	0.00412 (18)	0.00801 (19)
N1	0.0114 (7)	0.0125 (7)	0.0120 (7)	0.0009 (6)	0.0019 (6)	0.0007 (6)
N3	0.0182 (8)	0.0151 (8)	0.0153 (8)	−0.0011 (7)	0.0018 (7)	0.0025 (7)
N4	0.0160 (8)	0.0150 (8)	0.0131 (8)	−0.0031 (7)	0.0021 (7)	−0.0011 (6)
C1	0.0112 (8)	0.0115 (9)	0.0129 (8)	0.0006 (7)	−0.0005 (7)	0.0012 (7)
N2	0.0157 (11)	0.0167 (12)	0.0149 (9)	−0.0025 (9)	−0.0003 (7)	−0.0017 (9)
C2	0.0151 (13)	0.0221 (14)	0.0206 (14)	−0.0034 (11)	0.0028 (11)	−0.0018 (12)
C6	0.0201 (15)	0.0254 (16)	0.0205 (17)	−0.0040 (12)	−0.0041 (14)	0.0039 (13)
C7	0.0229 (15)	0.0231 (16)	0.0267 (18)	0.0001 (13)	0.0009 (13)	−0.0114 (15)
C3	0.019 (3)	0.025 (4)	0.0216 (18)	−0.009 (2)	0.003 (2)	0.002 (2)
N2A	0.0157 (11)	0.0167 (12)	0.0149 (9)	−0.0025 (9)	−0.0003 (7)	−0.0017 (9)
C2A	0.011 (4)	0.026 (5)	0.020 (4)	−0.001 (3)	0.000 (3)	−0.005 (4)
C6A	0.015 (4)	0.016 (4)	0.024 (6)	−0.003 (3)	−0.014 (4)	0.010 (4)
C7A	0.029 (5)	0.037 (6)	0.009 (4)	−0.004 (5)	−0.003 (4)	−0.008 (4)
C3A	0.019 (3)	0.025 (4)	0.0216 (18)	−0.009 (2)	0.003 (2)	0.002 (2)
C4	0.0291 (12)	0.0219 (11)	0.0205 (11)	−0.0029 (10)	0.0111 (10)	0.0014 (9)
C5	0.0372 (14)	0.0226 (11)	0.0131 (10)	−0.0073 (10)	0.0019 (9)	−0.0021 (9)
C8	0.0285 (13)	0.0262 (12)	0.0288 (13)	0.0048 (10)	0.0035 (10)	0.0143 (10)
C9	0.0214 (11)	0.0251 (12)	0.0223 (11)	−0.0091 (9)	0.0021 (9)	−0.0048 (9)
C10	0.0252 (11)	0.0167 (10)	0.0246 (11)	0.0027 (9)	0.0041 (10)	−0.0005 (9)
Cl2	0.01806 (17)	0.01806 (17)	0.01806 (17)	−0.00298 (19)	0.00298 (19)	−0.00298 (19)
O17	0.0189 (8)	0.0507 (13)	0.0273 (10)	−0.0060 (9)	0.0084 (7)	−0.0053 (9)
O18	0.0376 (8)	0.0376 (8)	0.0376 (8)	0.0064 (9)	−0.0064 (9)	0.0064 (9)
Cl1	0.01537 (15)	0.01537 (15)	0.01537 (15)	0.00089 (18)	−0.00089 (18)	0.00089 (18)
O15	0.0242 (6)	0.0242 (6)	0.0242 (6)	0.0057 (7)	−0.0057 (7)	0.0057 (7)
O16	0.0212 (8)	0.0222 (8)	0.0210 (8)	−0.0043 (7)	−0.0026 (7)	−0.0010 (7)
Cl3	0.01791 (17)	0.01791 (17)	0.01791 (17)	0.0027 (2)	−0.0027 (2)	−0.0027 (2)
O10	0.0336 (10)	0.0234 (9)	0.0314 (10)	0.0119 (8)	−0.0096 (8)	−0.0059 (8)
O20	0.0383 (9)	0.0383 (9)	0.0383 (9)	−0.0054 (9)	0.0054 (9)	0.0054 (9)

Geometric parameters (Å, º) top

Zn—N2	2.081 (10)	C2A—H2D	0.9900
Zn—N4	2.0877 (18)	C6A—H6A1	0.9800
Zn—N2A	2.09 (3)	C6A—H6A2	0.9800
Zn—N3	2.1592 (19)	C6A—H6A3	0.9800
Zn—N1	2.2053 (18)	C7A—H7D	0.9800
Zn—S	2.3792 (6)	C7A—H7E	0.9800
S—C1	1.710 (2)	C7A—H7F	0.9800
N1—C1ⁱ	1.342 (3)	C3A—H3A1	0.9900
N1—C1	1.358 (3)	C3A—H3A2	0.9900
N3—C8	1.472 (3)	C4—C5	1.512 (4)
N3—C3	1.473 (13)	C4—H4A	0.9900
N3—C4	1.477 (3)	C4—H4B	0.9900
N3—C3A	1.51 (5)	C5—H5A	0.9900
N4—C9	1.474 (3)	C5—H5B	0.9900
N4—C5	1.479 (3)	C8—H8A	0.9800
N4—C10	1.485 (3)	C8—H8B	0.9800
C1—N1ⁱⁱ	1.342 (3)	C8—H8C	0.9800
N2—C2	1.485 (6)	C9—H9A	0.9800
N2—C6	1.485 (6)	C9—H9B	0.9800
N2—C7	1.488 (6)	C9—H9C	0.9800
C2—C3	1.505 (13)	C10—H10A	0.9800
C2—H2A	0.9900	C10—H10B	0.9800
C2—H2B	0.9900	C10—H10C	0.9800
C6—H6A	0.9800	Cl2—O17ⁱⁱⁱ	1.4357 (19)
C6—H6B	0.9800	Cl2—O17^iv	1.4357 (19)
C6—H6C	0.9800	Cl2—O17	1.4357 (19)
C7—H7A	0.9800	Cl2—O18	1.438 (4)
C7—H7B	0.9800	Cl1—O15	1.435 (3)
C7—H7C	0.9800	Cl1—O16	1.4448 (17)
C3—H3A	0.9900	Cl1—O16ⁱⁱⁱ	1.4448 (17)
C3—H3B	0.9900	Cl1—O16^iv	1.4448 (17)
N2A—C6A	1.481 (16)	Cl3—O20	1.434 (4)
N2A—C2A	1.483 (16)	Cl3—O10^v	1.4386 (19)
N2A—C7A	1.484 (16)	Cl3—O10^vi	1.4386 (19)
C2A—C3A	1.53 (5)	Cl3—O10	1.4386 (19)
C2A—H2C	0.9900

N2—Zn—N4	121.56 (15)	H2C—C2A—H2D	107.7
N2—Zn—N2A	3.4 (6)	N2A—C6A—H6A1	109.5
N4—Zn—N2A	125.0 (5)	N2A—C6A—H6A2	109.5
N2—Zn—N3	85.10 (16)	H6A1—C6A—H6A2	109.5
N4—Zn—N3	85.50 (7)	N2A—C6A—H6A3	109.5
N2A—Zn—N3	85.8 (4)	H6A1—C6A—H6A3	109.5
N2—Zn—N1	98.43 (15)	H6A2—C6A—H6A3	109.5
N4—Zn—N1	98.90 (7)	N2A—C7A—H7D	109.5
N2A—Zn—N1	97.3 (4)	N2A—C7A—H7E	109.5
N3—Zn—N1	171.68 (7)	H7D—C7A—H7E	109.5
N2—Zn—S	115.99 (14)	N2A—C7A—H7F	109.5
N4—Zn—S	122.34 (6)	H7D—C7A—H7F	109.5
N2A—Zn—S	112.5 (4)	H7E—C7A—H7F	109.5
N3—Zn—S	103.04 (5)	N3—C3A—C2A	109 (3)
N1—Zn—S	68.63 (5)	N3—C3A—H3A1	110.0
C1—S—Zn	80.85 (7)	C2A—C3A—H3A1	110.0
C1ⁱ—N1—C1	117.0 (2)	N3—C3A—H3A2	110.0
C1ⁱ—N1—Zn	147.22 (15)	C2A—C3A—H3A2	110.0
C1—N1—Zn	95.61 (13)	H3A1—C3A—H3A2	108.4
C8—N3—C3	108.6 (4)	N3—C4—C5	110.0 (2)
C8—N3—C4	110.7 (2)	N3—C4—H4A	109.7
C3—N3—C4	113.4 (3)	C5—C4—H4A	109.7
C8—N3—C3A	116.0 (16)	N3—C4—H4B	109.7
C3—N3—C3A	10.0 (16)	C5—C4—H4B	109.7
C4—N3—C3A	103.7 (14)	H4A—C4—H4B	108.2
C8—N3—Zn	114.57 (15)	N4—C5—C4	111.5 (2)
C3—N3—Zn	105.1 (5)	N4—C5—H5A	109.3
C4—N3—Zn	104.47 (13)	C4—C5—H5A	109.3
C3A—N3—Zn	106.3 (17)	N4—C5—H5B	109.3
C9—N4—C5	110.32 (19)	C4—C5—H5B	109.3
C9—N4—C10	108.26 (19)	H5A—C5—H5B	108.0
C5—N4—C10	110.4 (2)	N3—C8—H8A	109.5
C9—N4—Zn	110.29 (14)	N3—C8—H8B	109.5
C5—N4—Zn	104.01 (14)	H8A—C8—H8B	109.5
C10—N4—Zn	113.49 (15)	N3—C8—H8C	109.5
N1ⁱⁱ—C1—N1	122.9 (2)	H8A—C8—H8C	109.5
N1ⁱⁱ—C1—S	122.48 (16)	H8B—C8—H8C	109.5
N1—C1—S	114.58 (16)	N4—C9—H9A	109.5
C2—N2—C6	109.2 (5)	N4—C9—H9B	109.5
C2—N2—C7	110.6 (5)	H9A—C9—H9B	109.5
C6—N2—C7	107.5 (5)	N4—C9—H9C	109.5
C2—N2—Zn	105.2 (4)	H9A—C9—H9C	109.5
C6—N2—Zn	114.9 (4)	H9B—C9—H9C	109.5
C7—N2—Zn	109.5 (4)	N4—C10—H10A	109.5
N2—C2—C3	111.0 (5)	N4—C10—H10B	109.5
N2—C2—H2A	109.4	H10A—C10—H10B	109.5
C3—C2—H2A	109.4	N4—C10—H10C	109.5
N2—C2—H2B	109.4	H10A—C10—H10C	109.5
C3—C2—H2B	109.4	H10B—C10—H10C	109.5
H2A—C2—H2B	108.0	O17ⁱⁱⁱ—Cl2—O17^iv	109.27 (10)
N3—C3—C2	111.7 (8)	O17ⁱⁱⁱ—Cl2—O17	109.27 (10)
N3—C3—H3A	109.3	O17^iv—Cl2—O17	109.27 (10)
C2—C3—H3A	109.3	O17ⁱⁱⁱ—Cl2—O18	109.67 (10)
N3—C3—H3B	109.3	O17^iv—Cl2—O18	109.67 (10)
C2—C3—H3B	109.3	O17—Cl2—O18	109.67 (10)
H3A—C3—H3B	107.9	O15—Cl1—O16	109.60 (8)
C6A—N2A—C2A	112.3 (15)	O15—Cl1—O16ⁱⁱⁱ	109.60 (8)
C6A—N2A—C7A	107.7 (15)	O16—Cl1—O16ⁱⁱⁱ	109.35 (8)
C2A—N2A—C7A	110.1 (15)	O15—Cl1—O16^iv	109.60 (8)
C6A—N2A—Zn	110.0 (14)	O16—Cl1—O16^iv	109.35 (8)
C2A—N2A—Zn	103.5 (13)	O16ⁱⁱⁱ—Cl1—O16^iv	109.35 (8)
C7A—N2A—Zn	113.2 (14)	O20—Cl3—O10^v	109.60 (10)
N2A—C2A—C3A	113.5 (19)	O20—Cl3—O10^vi	109.60 (10)
N2A—C2A—H2C	108.9	O10^v—Cl3—O10^vi	109.34 (10)
C3A—C2A—H2C	108.9	O20—Cl3—O10	109.60 (10)
N2A—C2A—H2D	108.9	O10^v—Cl3—O10	109.34 (10)
C3A—C2A—H2D	108.9	O10^vi—Cl3—O10	109.34 (10)

N2—Zn—S—C1	85.95 (18)	Zn—S—C1—N1	5.26 (15)
N4—Zn—S—C1	−90.23 (10)	N4—Zn—N2—C2	−62.8 (3)
N2A—Zn—S—C1	86.0 (5)	N2A—Zn—N2—C2	120 (10)
N3—Zn—S—C1	176.83 (9)	N3—Zn—N2—C2	18.9 (3)
N1—Zn—S—C1	−3.16 (9)	N1—Zn—N2—C2	−168.7 (3)
N2—Zn—N1—C1ⁱ	63.9 (3)	S—Zn—N2—C2	121.0 (3)
N4—Zn—N1—C1ⁱ	−60.1 (3)	N4—Zn—N2—C6	57.3 (4)
N2A—Zn—N1—C1ⁱ	67.2 (5)	N2A—Zn—N2—C6	−120 (10)
N3—Zn—N1—C1ⁱ	178.4 (4)	N3—Zn—N2—C6	139.0 (4)
S—Zn—N1—C1ⁱ	178.6 (3)	N1—Zn—N2—C6	−48.6 (4)
N2—Zn—N1—C1	−110.74 (19)	S—Zn—N2—C6	−118.9 (3)
N4—Zn—N1—C1	125.29 (13)	N4—Zn—N2—C7	178.4 (3)
N2A—Zn—N1—C1	−107.5 (5)	N2A—Zn—N2—C7	1 (9)
N3—Zn—N1—C1	3.8 (6)	N3—Zn—N2—C7	−100.0 (3)
S—Zn—N1—C1	3.95 (11)	N1—Zn—N2—C7	72.4 (3)
N2—Zn—N3—C8	126.7 (2)	S—Zn—N2—C7	2.2 (4)
N4—Zn—N3—C8	−111.00 (18)	C6—N2—C2—C3	−166.9 (6)
N2A—Zn—N3—C8	123.4 (5)	C7—N2—C2—C3	75.0 (8)
N1—Zn—N3—C8	11.3 (6)	Zn—N2—C2—C3	−43.1 (6)
S—Zn—N3—C8	11.18 (18)	C8—N3—C3—C2	−156.5 (4)
N2—Zn—N3—C3	7.6 (4)	C4—N3—C3—C2	80.0 (6)
N4—Zn—N3—C3	129.9 (3)	C3A—N3—C3—C2	65 (12)
N2A—Zn—N3—C3	4.2 (6)	Zn—N3—C3—C2	−33.5 (6)
N1—Zn—N3—C3	−107.8 (6)	N2—C2—C3—N3	53.9 (7)
S—Zn—N3—C3	−107.9 (3)	N2—Zn—N2A—C6A	21 (9)
N2—Zn—N3—C4	−112.0 (2)	N4—Zn—N2A—C6A	18.4 (13)
N4—Zn—N3—C4	10.24 (16)	N3—Zn—N2A—C6A	99.9 (10)
N2A—Zn—N3—C4	−115.4 (5)	N1—Zn—N2A—C6A	−87.9 (10)
N1—Zn—N3—C4	132.5 (5)	S—Zn—N2A—C6A	−157.7 (9)
S—Zn—N3—C4	132.41 (15)	N2—Zn—N2A—C2A	−99 (10)
N2—Zn—N3—C3A	−2.7 (14)	N4—Zn—N2A—C2A	−101.8 (8)
N4—Zn—N3—C3A	119.5 (14)	N3—Zn—N2A—C2A	−20.3 (8)
N2A—Zn—N3—C3A	−6.1 (15)	N1—Zn—N2A—C2A	151.9 (8)
N1—Zn—N3—C3A	−118.2 (15)	S—Zn—N2A—C2A	82.1 (9)
S—Zn—N3—C3A	−118.3 (14)	N2—Zn—N2A—C7A	142 (10)
N2—Zn—N4—C9	−142.4 (2)	N4—Zn—N2A—C7A	139.0 (9)
N2A—Zn—N4—C9	−142.2 (6)	N3—Zn—N2A—C7A	−139.5 (11)
N3—Zn—N4—C9	136.14 (16)	N1—Zn—N2A—C7A	32.8 (11)
N1—Zn—N4—C9	−36.75 (16)	S—Zn—N2A—C7A	−37.1 (12)
S—Zn—N4—C9	33.54 (17)	C6A—N2A—C2A—C3A	−73 (3)
N2—Zn—N4—C5	99.3 (2)	C7A—N2A—C2A—C3A	167 (2)
N2A—Zn—N4—C5	99.5 (6)	Zn—N2A—C2A—C3A	46 (2)
N3—Zn—N4—C5	17.86 (16)	C8—N3—C3A—C2A	−98 (2)
N1—Zn—N4—C5	−155.02 (15)	C3—N3—C3A—C2A	−54 (11)
S—Zn—N4—C5	−84.74 (16)	C4—N3—C3A—C2A	140.8 (18)
N2—Zn—N4—C10	−20.8 (2)	Zn—N3—C3A—C2A	31 (2)
N2A—Zn—N4—C10	−20.5 (6)	N2A—C2A—C3A—N3	−54 (3)
N3—Zn—N4—C10	−102.20 (16)	C8—N3—C4—C5	87.2 (2)
N1—Zn—N4—C10	84.91 (16)	C3—N3—C4—C5	−150.5 (6)
S—Zn—N4—C10	155.20 (13)	C3A—N3—C4—C5	−147.8 (18)
C1ⁱ—N1—C1—N1ⁱⁱ	−2.8 (4)	Zn—N3—C4—C5	−36.6 (2)
Zn—N1—C1—N1ⁱⁱ	173.88 (18)	C9—N4—C5—C4	−162.5 (2)
C1ⁱ—N1—C1—S	177.64 (10)	C10—N4—C5—C4	77.9 (3)
Zn—N1—C1—S	−5.63 (16)	Zn—N4—C5—C4	−44.2 (2)
Zn—S—C1—N1ⁱⁱ	−174.25 (19)	N3—C4—C5—N4	57.5 (3)

Symmetry codes: (i) y, z, x; (ii) z, x, y; (iii) z−1/2, −x+1/2, −y+1; (iv) −y+1/2, −z+1, x+1/2; (v) y−1/2, −z+3/2, −x+1; (vi) −z+1, x+1/2, −y+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O17	0.99	2.85	3.659 (4)	140
C6—H6C···O17	0.98	2.55	3.475 (4)	157
C6—H6C···O17	0.98	2.55	3.475 (4)	157
C7—H7A···O17	0.98	2.91	3.752 (4)	144
C2A—H2D···O17	0.99	2.97	3.805 (10)	143
C2A—H2D···O17	0.99	2.97	3.805 (10)	143
C6A—H6A3···O17	0.98	2.50	3.413 (10)	155
C6A—H6A3···O17	0.98	2.50	3.413 (10)	155
C7A—H7F···O17	0.98	2.94	3.772 (12)	143
C7A—H7F···O17	0.98	2.94	3.772 (12)	143
C6A—H6A2···O10^vi	0.98	2.67	3.642 (14)	170
C2—H2B···O10^vi	0.99	2.42	3.358 (4)	158
C4—H4B···O10^vi	0.99	2.52	3.506 (4)	177
C5—H5B···O18^vi	0.99	2.79	3.515 (3)	130
C10—H10B···O10^vi	0.98	2.69	3.652 (3)	167
C2A—H2C···O16^iv	0.99	2.59	3.402 (11)	140
C2—H2A···O17^iv	0.99	2.68	3.411 (4)	131
C8—H8C···O16^iv	0.98	2.83	3.556 (4)	132
C3—H3B···O16^iv	0.99	2.45	3.417 (9)	165
C7—H7C···O20^vii	0.98	2.71	3.438 (4)	131
C7A—H7E···O20^vii	0.98	2.61	2.888 (10)	96
C7—H7C···O20ⁱⁱⁱ	0.98	2.71	3.438 (4)	131
C7—H7C···O20ⁱⁱⁱ	0.98	2.71	3.438 (4)	131
C7—H7C···O20^viii	0.98	2.71	3.438 (4)	131
C7—H7C···O20^viii	0.98	2.71	3.438 (4)	131
C7A—H7F···O10^viii	0.98	2.78	3.547 (10)	135
C7—H7A···O10^viii	0.98	3.04	3.768 (4)	132
C5—H5B···O18^ix	0.99	2.79	3.515 (3)	130
C4—H4A···O17^ix	0.99	2.53	3.265 (3)	131
C4—H4B···O10^v	0.99	2.61	3.289 (3)	126
C5—H5B···O18^x	0.99	2.79	3.515 (3)	130
C10—H10C···Sⁱ	0.98	2.98	3.900 (3)	157

Symmetry codes: (i) y, z, x; (iii) z−1/2, −x+1/2, −y+1; (iv) −y+1/2, −z+1, x+1/2; (v) y−1/2, −z+3/2, −x+1; (vi) −z+1, x+1/2, −y+3/2; (vii) −x+1/2, −y+1, z−1/2; (viii) −y+1, z−1/2, −x+1/2; (ix) −x+1/2, −y+1, z+1/2; (x) y, z, x+1.

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